1,3-Dihydroisobenzofuran → Phthalaldehyde

HRID 1532478Notes

Reaction equation

HRID 1532478 reaction equation
C1OCC2C1=CC=CC=2.ON1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].[N]=O>C(#N)C>[CH:12](=[O:21])[C:13]1[C:14](=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 103271,3-Dihydroisobenzofuran2×HCID 10665N-HydroxyphthalimideHCID 145068Nitric Oxide

Product 1

HCID 4807PhthalaldehydeYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 10 mmol of phthalan (isocoumaran), 1 mmol of N-hydroxyphthalimide, and 5 ml of acetonitrile was introduced 120 mmol of nitrogen monoxide, and the resultant mixture was stirred at 60° C. for 8 hours. Isolation of products in the reaction mixture by column chromatography on a silica gel revealed that phthalan was converted, at a rate of 99%, into phthalaldehyde (yield: 94%).

Sources & evidence

ORD record
ord-96a709a5b52d4334a77ac2a4c4910717
Source dataset
uspto-grants-2001_03
Patent number
US06201156B1

Reaction notes

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